Issue 14, 2024

Merging 2,3-butanedione and N-hydroxysuccinimide as visible-light-enabled hydrogen atom transfer catalysts for C[double bond, length as m-dash]C double bond cleavage of 2-cyanoaryl acrylamides toward the synthesis of 4-amino-2-quinolones

Abstract

The C[double bond, length as m-dash]C double bond cleavage of 2-cyanoaryl acrylamides through merging 2,3-butanedione and N-hydroxysuccinimide as visible-light-enabled hydrogen atom transfer catalysts is effectively established for generating functionalized 4-amino-2-quinolones under metal-free and redox neutral conditions. Detailed mechanism studies indicate that the solvent 1,3-dioxolane offers the crucial 1,3-dioxolan-2-yl radical facilitated by the in situ formed H-atom abstracting species, and 2-alkenyl-1,3-dioxolane is probably another product in this photocatalytic protocol.

Graphical abstract: Merging 2,3-butanedione and N-hydroxysuccinimide as visible-light-enabled hydrogen atom transfer catalysts for C [[double bond, length as m-dash]] C double bond cleavage of 2-cyanoaryl acrylamides toward the synthesis of 4-amino-2-quinolones

Supplementary files

Article information

Article type
Research Article
Submitted
12 Mar 2024
Accepted
19 May 2024
First published
20 May 2024

Org. Chem. Front., 2024,11, 3855-3860

Merging 2,3-butanedione and N-hydroxysuccinimide as visible-light-enabled hydrogen atom transfer catalysts for C[double bond, length as m-dash]C double bond cleavage of 2-cyanoaryl acrylamides toward the synthesis of 4-amino-2-quinolones

J. Huang, F. Zhu, J. Wen, J. Xu, J. Yuan and W. Chen, Org. Chem. Front., 2024, 11, 3855 DOI: 10.1039/D4QO00458B

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